In the FX series Love Story, Carolyn Bessette worries that if her relationship with John F. Kennedy Jr. doesn’t last, she’ll always be remembered as simply his ex-girlfriend.
Daryl Hannah, already a popular actress by 1988, wasn’t particularly worried about the public’s reaction to her relationship with a Kennedy. While the media was fascinated by the couple—and that interest has resurfaced with the new Ryan Murphy series about John F. Kennedy Jr. and Carolyn Bessette—it didn’t seem to matter much once they broke up in 1994.
This happens a couple of years after John and Carolyn first met. Daryl, played by Dree Hemingway (whose mother is Mariel Hemingway and great-grandfather was Ernest Hemingway), mostly exists to create challenges for the central relationship in the show.
Though the show didn’t contact Daryl Hannah to get her perspective on the story—which was based on real events—producer Nina Jacobson explained to Gold Derby that they approached the narrative with empathy. Because the audience is meant to support John and Carolyn, Hannah’s character ended up positioned as an obstacle to their success.
Daryl was a famous actor, so unlike Carolyn—who worked as a sales associate at Calvin Klein, assisting celebrities—he wasn’t bothered by the attention from the paparazzi or the tabloids when it came to his relationships.
Nina explained that even though she seems very different from John, they still acknowledge her understanding of his world, something Carolyn lacks. She’s able to easily navigate his social circles in a way Carolyn struggles with.
Still, dating JFK Jr. did come with a whole new level of attention.
Daryl expressed his frustration in a 1993 interview with Entertainment Weekly, saying, “It’s really getting to me how much I’m asked about it.” He recounted an experience from that morning where even his plumber brought it up, adding, “I just want to get my plumbing fixed! Can’t people talk about something else?”
Daryl Hannah, now 65 and known for films like Splash and Roxanne, first met John in the 1970s. They were both teenagers on family vacations in Saint Martin at the time. Although they lost touch, they spent much of the 1980s dating other people – John was with Christina Haag, among others, and Daryl lived with musician Jackson Browne.
John and Daryl ran into each other again at the 1988 wedding of John’s aunt, Lee Radziwill, and her new husband, Herbert Ross. Ross had recently directed Daryl in the movie Steel Magnolias.
Soon after John was named Sexiest Man Alive by People magazine in September, he was set up with Daryl by her stepfather, Jerrold Wexler, a film producer and political donor. They had an on-again, off-again relationship for the next six years, even while dating other people. In October 1992, John flew to California to be with Daryl after her breakup with Jackson, and then brought her back to New York with him.
He also began dating Carolyn that summer, but their relationship didn’t last, partly because she was discouraged to see news reports suggesting John and Daryl were getting back together.
While they were dating, there were rumors that Jacqueline Kennedy didn’t approve of the actress her son was seeing.
In a rare 2004 appearance on The Howard Stern Show, Daryl dismissed rumors of a feud with Jackie. She explained that people often speculate about the reasons for their breakup, and those guesses get repeated as if they were facts. “It has no bearing on reality whatsoever,” she stated, emphasizing the inaccuracies of the stories.
She said they had a very good relationship, but she didn’t want to share private details.
She’s remained deliberately vague about her relationship with John, never sharing specifics about what their time together was like.
According to Amelia Barlow, daughter of John Perry Barlow, Daryl was fantastic. In the 2024 book JFK Jr.: An Intimate Oral History, written by RoseMarie Terenzio and Liz McNeil, she described the relationship between the Wall Street actress and John as feeling like a fantastical adventure. She noted it seemed younger and perhaps a little naive compared to his relationship with Carolyn.
It was a really tough time around Jackie’s passing in 1994, and there was a lot going on behind the scenes. Just before she died, a tragic accident happened – Daryl’s dog was hit by a car while John was supposed to be watching him. He immediately flew to Los Angeles to deliver the dog’s ashes to Daryl. A close friend, Steve Gillon, shared with me that John was understandably upset about being asked to fly out for the dog’s memorial when his own mother was seriously ill with cancer. It was a lot of emotional strain for everyone involved, to say the least.
As a lifestyle expert, I’ve always found observing relationships fascinating, and Carole Radziwill shared a particularly poignant detail with me about the memorial service for Jackie Kennedy. She told me she actually took Daryl shopping for a ‘proper funeral dress’ to wear. It was a heartbreaking moment, and she observed that the distance between John and Jackie was palpable. She felt, and I think rightly so, that Jackie understood at that moment their relationship was ending.
As I understand it from J. Randy Taraborrelli’s book, The Kennedy Heirs, John confided in friends about a month after his mother’s passing that he and Daryl really should have tied the knot much sooner. It was clearly something he was thinking about and regretting at a difficult time.
Carole mentioned that when she married John’s cousin, Anthony Radziwill, in August 1994, he had secretly started dating Carolyn again.
Despite being at the center of a very public romance, Daryl continued living her life after the relationship ended. She didn’t attend John and Carolyn’s funeral in 1999, and she hasn’t ever spoken negatively about her former partner in public.
She eventually became just as well-known for her work as an environmental activist as she was for her acting career. The former Kill Bill star famously promoted alternative fuels after converting her 1983 Chevy El Camino to run on biodiesel, and she often joked that the car smelled like food – either donuts or French fries – because it used vegetable oil as fuel.
Daryl shared with The Times in 2005 that her parents’ divorce when she was seven years old was a turning point. It made her realize that life wasn’t as simple as she’d been taught, and she wanted to understand how the world really worked. She’s always believed it’s possible to live in harmony with nature without extreme self-denial or a harsh, minimalist lifestyle.
She was arrested twice – in 2011 and 2013 – while protesting the Keystone XL pipeline in Washington, D.C.
In 2017, Daryl joined other women in accusing Harvey Weinstein of sexual misconduct. She told Ronan Farrow of the New Yorker that after she spoke about alleged experiences with the producer in the mid-2000s, her career suffered immediate consequences.
Honestly, it just kills me how people treat her. It doesn’t matter if she’s a huge star, young or older, whether she speaks out or stays quiet – nobody listens! It’s worse than that, though. They don’t just dismiss what she says, they tear her down, criticize everything she does, and actually blame her for it all! It’s absolutely infuriating to watch.
I’ve always admired her for being so private – she really only spoke to the press when it was about her work. But she felt it was incredibly important to share what happened to her. She said she had a real responsibility to stand with other women who’ve gone through even worse experiences, and I think that’s amazing.
Daryl Hannah generally kept her personal life private, but after her relationship with John F. Kennedy Jr., she dated Val Kilmer, who later wrote in his memoir, I’m Your Huckleberry, that she caused him the most heartbreak. She then married Neil Young in 2018; it was her first marriage, and his third.
In 2023, she received a Grammy nomination for Best Musical Film for directing the documentary A Band a Brotherhood a Barn. The film focuses on her husband and his band, Crazy Horse.
She recently directed the concert film Coastal. In an interview with the Telluride Times in April 2025, she explained that she aimed to showcase Neil’s genuine, open, and vulnerable side – qualities rarely seen in his performances. She wanted to capture his authenticity as a person, musician, and performer.
When Daryl directed Neil in the 2018 Netflix film Paradox, Neil spoke to The Independent about his wife, saying he wasn’t concerned with her performance because he knew she would deliver something excellent. He felt people often focused more on her appearance than on her talent and intelligence.
Discover what the documentary Love Story: John F. Kennedy Jr. & Carolyn Bessette accurately portrays—and where it takes creative license—regarding JFK Jr.’s relationship with Daryl, and other details.
In the movie Love Story: John F. Kennedy Jr. & Carolyn Bessette, Carolyn (played by Sarah Pidgeon) advises Annette Bening (played by Megan Channell) to wear a Calvin Klein suit to the Bugsy premiere instead of the dress the designer chose for her.
As a stylist, I’ve always been fascinated by Carolyn Bessette-Kennedy’s impact. While it’s debated if she specifically styled looks for Anette, Diane Sawyer, and Blaire Trump, a fascinating 1996 New York Times piece revealed she was Calvin Klein’s go-to for dressing their celebrity clients. She really had a knack for making those women look and feel incredible!
According to Paul Wilmott, who was Calvin Klein’s VP of public relations at the time, she expertly helped customers choose clothes, offering advice on what suited them and how to create complete outfits. He noted that she was incredibly successful, selling millions of dollars worth of clothing over the years.
In a memorable scene from Love Story, Carolyn demonstrates her skill by suggesting to Calvin (played by Alessandro Nivola) that he feature Kate Moss in an advertising campaign.
Carolyn was one of the first people to recognize Kate Moss’s potential, and she played a key role in shaping the Calvin Klein image of the 1990s.
In the movie Love Story, Calvin brings Carolyn and John together at a charity event in 1992, and they immediately feel a connection. However, Carolyn playfully declines to give Calvin her phone number, reminding him that she works where he can easily find her.
“He was simply bored,” Carolyn explained to her friends at the nightclub, just as Michael Bergin, who they playfully called the “sexy doorman” (and was actually Noah Fearnley), walked up.
I couldn’t believe it when John just showed up at Calvin Klein, wanting a private fitting with Carolyn! Then, he had the nerve to ask her out to dinner. Honestly, after he left, everyone at work completely lost it – it was total chaos!
According to Elizabeth Beller’s 2024 biography, Once Upon a Time: The Captivating Life of Carolyn Bessette-Kennedy, John F. Kennedy Jr. and Carolyn Bessette-Kennedy first met in the spring of 1992. John was at Calvin Klein for a private fitting, and her coworkers were reportedly very excited. He then asked Carolyn to join him at a gala, as MJ Bettenhausen told Beller. However, Carolyn mistakenly believed another woman was his date and declined when he invited her to an after-party.
Carolyn and Michael, a model who previously worked as a hotel doorman, briefly dated starting in the fall of 1992, but their relationship was more casual than serious, according to Beller’s book.
In his 2004 book, The Other Man, Bergin claimed he was sexually involved with Carolyn throughout her entire relationship with John, even until her death. However, according to Beller, many of Carolyn’s friends doubted this claim.
In the movie Love Story, Carolyn is waiting at an Indian restaurant for John. After about 20 minutes, just as she’s about to leave, he arrives riding his bicycle.
He accidentally left the car unlocked, and when they finished their long date, they discovered it had been stolen. This meant he ended up walking Carolyn home instead.
He said he wished he hadn’t felt so rushed as they reached her door. She asked what he meant, and he kissed her. He then wondered if he’d see her again, and she replied that she’d enjoyed their evening together before ending the date.
In real life, John and this person likely went on a first date, and it’s possible he biked there and was a little late. However, the image of them connecting over drinks was probably staged for the show.
Daryl Hannah (played by Dree Hemingway) is at John’s apartment when he returns home. He’s just been telling his cousin and best friend, Anthony Radziwill (Erich Bergen), that all he wants to do is call Carolyn.
He’s planning to take Daryl to a wedding in October 1993 – his cousin Edward Kennedy Jr.’s – despite his mother, Jacqueline Kennedy, being unhappy about it. Meanwhile, Carolyn discovers through a tabloid magazine that the man who seemed so interested in her is actually getting back together with his famous ex-girlfriend.
Okay, so things are getting interesting with John and Carolyn. He’s been really pursuing her with flowers, and then, when they ran into each other at an event, he dramatically confessed he was struggling because he thought she hated him. Honestly, it was a bit much! Her response was perfect though – she simply told him she didn’t even know him well enough to have that strong of a feeling. It’s a classic case of someone projecting, really. It just shows how important it is to communicate honestly and not assume things!
The unexpected meeting was a striking way to reveal that the star of Splash was joining the cast of Love Story. However, producers didn’t consult with Daryl, who has been married to Neil Young since 2018.
Producer Nina Jacobson explained to Gold Derby that they focus on understanding the core of each character. She said it’s difficult to push specific viewpoints when interviewing the people who inspired those characters, so they generally avoid doing so except in unusual situations.
According to Jacobson, Daryl acts as a challenge to what the story is trying to achieve, but the writers still aim to highlight her understanding of the celebrity lifestyle, something Carolyn lacks.
When John walks in and sees Daryl with her eccentric friends, it’s a clear signal that major changes are coming. She ultimately breaks up with him, forcing him to think about what he truly desires.
Daryl promised she would return for her dog, Hank. However, while John was walking Hank, he was distracted by a fan asking for an autograph. He accidentally dropped the leash, and tragically, Hank was hit by a taxi and killed. John then flew to Los Angeles to deliver Hank’s ashes to Daryl.
According to the 2024 book JFK Jr.: An Intimate Oral Biography by RoseMarie Terenzio and Liz McNeil, John F. Kennedy Jr.’s friend, Sasha Chermayeff, recounted that Kennedy’s dog, Hank, ran into traffic in Central Park and was hit by a car in May 1994.
According to his friend Steven Gillon, he traveled to Los Angeles to bury a dog. While he was there, his mother’s health suddenly worsened. He felt angry that Daryl had made him attend the dog’s funeral when his mother was seriously ill with cancer.
In the movie Love Story, Jackie (played by Naomi Watts) leaves a voicemail for John while he’s flying, then collapses at home. This scene was created for dramatic impact, but it’s also meant to emphasize how severely ill she was after being diagnosed with non-Hodgkin’s lymphoma in December 1993. She passed away on May 19, 1994.
John and Carolyn hadn’t seen each other since the disastrous gala until they ran into each other again at a fundraiser on May 18, 1992.
Oh my gosh, it’s just so tragic and romantic! They totally clicked right away and had this amazing summer fling, but then things faded a bit for almost two years, according to everything I’ve read. It’s like fate intervened – they didn’t really get together, truly together, until after Jackie was gone. It’s just… heartbreaking and perfect all at once!
As a lifestyle expert, I can tell you that behind the scenes, this couple’s relationship was a bit more complicated than we could show on TV! It was a lot of back and forth, honestly. But we made a creative decision to move the story forward, because we felt the audience would lose interest if we dwelled on all the ups and downs of their early romance. We wanted to keep things moving and focus on the bigger picture.
When he brings Carolyn home to his loft for the first time, John realizes he forgot his keys.
Although it looked good on television, John in real life was often forgetful and frequently lost his keys and wallet. This habit later made Carolyn hesitant to fly with him by himself after he earned his pilot’s license.
Beyond that hint of what’s to come, John doesn’t mention to Carolyn that the party he invites her to is actually a formal birthday dinner for his sister, Caroline Kennedy Schlossberg.
Let me clear something up, because this happens all the time in relationships! When Carolyn was getting a little worried, I explained that John just has a tendency to be forgetful. It’s easy to jump to conclusions, but I quickly reassured her it wasn’t about him unexpectedly having guests – just a classic case of him being a bit absentminded.
According to Carole Radziwill’s memoir, What Remains, John introduced Carolyn to his sister on her 37th birthday—November 27, 1994—at a party held at Carolyn’s Park Avenue apartment, rather than a formal dinner.
The former Real Housewives star, who attended with Anthony and was excited to see Carolyn, described her friend entering the secure room looking beautiful and unapologetically herself, and acting warmly and spontaneously.
Caroline embraced John and greeted Carolyn with a warm ‘So nice to meet you,’ according to Carole. Afterward, Carolyn’s friends offered polite smiles before turning their attention back to John.
Contrary to initial impressions, Carolyn and Caroline actually hit it off immediately, according to Beller’s book, Once Upon a Time. Someone who saw them having lunch described them as enjoying each other’s company, with lively conversation and plenty of laughter.
After playing touch football with friends, John discovered a letter in his gym bag suggesting Carolyn had used her boss, Calvin Klein, to set up a date with him, hoping to win him over. When Carolyn visited later, John confronted her about the letter, and she was deeply hurt that he’d believe such a thing, so she left.
After what felt like a long wait, he finally came to her apartment and admitted he’d made a mistake. This honest conversation led to him confessing his love for her – it was the first time he’d said those words.
According to Beller, John did receive a letter outlining claims about Carolyn’s active social life and relationships, but this happened relatively early in their dating history. The book states that after dating in the summer of 1992, John abruptly ended things after reading the letter, and Carolyn didn’t accept his apologies for over a year.
John proposed to Carolyn while they were rowing a boat, shortly after she’d met his entire family for the first time in Hyannis Port. This included Ethel Kennedy, a powerful and respected figure played by Jessica Harper.
Carolyn said she needs some time to consider it, explaining that they have some really important things to talk over first. As a long-time supporter, I understand needing to be thorough, and I’m happy to wait until they’ve had a chance to discuss everything properly.
Terenzio says John proposed to Carolyn while they were on a trip to Martha’s Vineyard over the Fourth of July weekend in 1995. He proposed on a boat, saying, “Fishing is so much better with a partner.”
He proposed with a diamond and sapphire eternity band. On the show, JFK Jr. claimed it had belonged to his mother, but actually, John asked Jackie’s close friend Maurice Tempelsman to create a ring that resembled her famous emerald and sapphire ring—often called the “swimming ring.” According to Terenzio, John gave Carolyn both rings.
According to a friend of John F. Kennedy Jr., Carolyn Bessette-Kennedy made him wait around three weeks before she responded to a proposal. While Gillon’s 2019 book, American Prince, states she didn’t explicitly say yes, she did wear an engagement ring and told friends they were planning a wedding. However, in an oral history, Terenzio recalls Carolyn telling her they became engaged over the holiday weekend.
Whether it was before or after they started dating, the couple was engaged for several months leading up to their well-known argument in Washington Square Park in 1996.
Carolyn was a trusted confidante of her boss, Calvin Klein, and also enjoyed a close friendship with his wife, photographer Kelly Klein.
In the movie Love Story, Kelly (played by Leila George) challenges Calvin when he tells her she’ll have to stop working for him because their relationship is becoming public—specifically after a New York Post cover announces JFK Jr.’s proposal—and he worries it will be a distraction.
Kelly retorted, “With all due respect, you’re hardly one to talk about keeping secrets.” Calvin replied, “You knew what you were getting into from the start.”
The designer invited Kelly to join her at a gala that evening, hinting that it would be their last time together – a clear sign they were breaking up.
Calvin and Kelly announced they were separating in August 1996. According to columnist Liz Smith, they released a statement saying they remained good friends and had decided to live separately, with mutual respect, and hoped to resolve any differences privately. Their divorce was finalized in 2006.
At 83 years old, Calvin has been with his partner, model Kevin Baker, for a decade. Baker is 46 years younger than him.
In the movie Love Story, Carolyn skips John’s press conference where he introduces George magazine. At the event, he reveals the first cover, which features Cindy Crawford playfully dressed as George Washington.
She watches on TV from home, having reluctantly agreed that John didn’t have a choice other than to issue a denial that he proposed, lest the rumors that she had left him hanging overshadow the George news.
Carolyn intentionally avoided the launch event on September 7, 1995. Terenzio, responsible for publicly denying John was engaged—after a photo of Carolyn’s ring caused rumors—explained that John and his partner, Michael Berman, believed her attendance would be a distraction, and that she didn’t mind not being there.
John’s friend, Sasha Chermayeff, recalled in an interview that Carolyn was deeply upset by John’s refusal to publicly acknowledge their engagement. Chermayeff believed this was an early indication of the challenges Carolyn would face in the relationship – a preview of what life with John would be like.
In the fifth episode, Carolyn and John have a heated fight while walking their dog, but the episode concludes with a tearful Carolyn saying yes to John’s marriage proposal.
The highly publicized fight between the couple on February 25, 1996, became well-known, and many details – like John appearing to remove Carolyn’s engagement ring, John crying on the curb, and their argument over the dog, with Carolyn famously declaring, “You’ve got my ring, you’re not getting my dog!” – were widely reported in the news.
The show centers around a fight sparked by John’s frustration over Carolyn rejecting his proposal. He angrily claims everything would be fine if she’d just accepted him, but they’d actually been engaged for around five months. The series reveals that Carolyn privately tried on the ring and seemed open to marrying him, but hadn’t formally said yes before the argument began.
In her interview, Terenzio remembered that she and her husband often argued because John’s friends were taking advantage of him.
At a wedding, they found themselves seated next to a reporter from the New York Times who was covering the event for the ‘Vows’ column. According to Terenzio, Carolyn believed it was unfair to put a friend in that position. She observed that while John’s Carolyn regretted the argument, she was also upset with him, feeling she had been trying to shield him from being exploited.
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2026-02-27 11:20